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A New Strategy for the Design of Water‐Soluble Synthetic Receptors: Specific Recognition of DNA Intercalators and Diamines. by Kenji Wada; Tadashi Mizutani; Hideki Matsuoka; Susumu Kitagawa is a Chemistry article available to read on EtoBox.

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## Abstract Water‐soluble zinc bisporphyrin receptors **1** and **2** having two Lewis acidic sites (zinc) in the hydrophobic environment consisting of alkyl chains and a bisporphyrin framework, and covered with hydrophilic exterior (twelve or eighteen carboxyl groups) were prepared. The receptors show high affinity for diamines and DNA intercalators in water where the binding constants __K__~a~ are of the order of 10^7^ and 10^8^ M^−1^, respectively. Diamines and DNA intercalators are bound to the receptor through different mechanisms. Diamines are bound through hydrophobic interactions and zinc–nitrogen interactions, while DNA intercalators are bound through hydrophobic interactions and charge‐transfer interactions. Flexible alkyl chains can make van der Waals contact with guests and create a hydrophobic environment around the bound guest by an induced‐fit‐type mechanism. For the binding of DNA intercalators, the following features are noteworthy: 1) Binding constants are similar between the zinc porphyrins and zinc‐free porphyrins; 2) the binding constant is larger for the guest having the lower LUMO; this indicates the important contribution of charge‐transfer interactions to b

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Author

Kenji Wada; Tadashi Mizutani; Hideki Matsuoka; Susumu Kitagawa

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); John Wiley & Sons Ltd.; Wiley (ISSN 0947-6539)

Published

2003

Language

EN

Field

Chemistry (Physical Sciences)